Grit + failure: How to actually help people fail fast and overcome.

We’ve all had that experience. It may come in the form of critical feedback, “You’re just not meeting expectations.” It may be the rejection letter, “You’re great… But there’s someone greater than you.” Or the classic, “It’s not you, it’s me. (But really it’s you and I’m just passive).” If you’re like me, these moments can leave you with a tinge of despair and general thinking that you suck. In other words…

Values vs. reality

Each week I have the opportunity to dive deep into the cultures of at least a dozen organizations. At some point I always ask to hear more about their company values.

Inevitably I hear something to the effect of fail fast. Act with urgency! Be quick, be smart, mess up and move on. On paper these values are compelling. Demystifying failures, encouraging learning, and challenging oneself to overcome, who wouldn’t want that environment?

But during the same week, I also hear mangers and IC’s of these same companies saying, “I don’t give feedback because I’m scared to let someone know they’ve messed up.” Or, “I don’t like to ask for feedback because I don’t want to know that I’m not meeting expectations.” It may also sound like this, “I don’t want to ask my manager a lot of questions because I don’t want them to think I don’t get it.”

Like any nerdy researcher I find myself asking, how can people live into the espoused values of a culture without the fear that comes with feeling like you (might) suck? And how can one actually fail fast and overcome the sucky feeling of sucking?

Grit for the long haul

I’ve been learning about the concept of grit lately. Many folks are familiar with a learning orientation or a mastery approach to one’s work and hobbies, made famous by Stanford researcher Carol Dweck (shameless plug for my colleague Roi’s practical article on growth mindset for managers!). Whereas a learning orientation can help us overcome challenges and failures that we may not have a level of competence for yet, grit takes learning postures to the next stage.

Angela Duckworth notes that grit is not just approaching life with a bent towards learning but also “having a passion to accomplish a particular top-level goal and the perseverance,” to push through the valleys. She also notes that the grittiest people have a passion for what they are pursuing and a commitment to the years of practice it may take to achieve that goal. In other words, grit may provide the impetus to push through the valleys and the moments of feeling like you suck. But grit only gets us so far if we are in an environment that does not encourage ones growth.

My failed singing career

While I was growing up, I grew quite a proclivity for singing. Nobody home? You better believe I was blaring whatever top charting female ballad I could get my hands on. For anyone who had ears to hear, I would sing. In my mind, I was beautifully harmonizing with Mariah, Aretha, and Christina.

In actuality, I was not. Not even close.

My family was ruthless, I mean honest, enough to provide the hard feedback that I might want to consider pursuing sports or school instead. However, despite their hard feedback, they were unrelenting in their provisions of opportunities for growth. They still sent me to musical theatre camp, my mom still taught me how to sign from my diaphragm, and most importantly, they still came to my performances. In other words, they showed up, and it meant everything. While I most certainly had the passion to keep singing, I eventually realized that singing was not my top-level goal, and rather a hobby of passion reserved for road trips.

What this story stirs for me is the desire to build environments where the values of failing fast are met with the actionable support that actually allows one to discover if they have grit. Or, if like me, they have other goals more worthy of their pursuit. So how do you build a fail fast environment? Here’s three places to start!

Keys to creating a safe fail fast environment

1. Build trust by being consistent: Trust is not a static state but an evolving process of consistent words and actions over time. An easy way to do this is to create consistent routines & rituals. Weekly lunches, consistent 1:1’s, and quarterly retreats all communicate the message that despite the chaotic ups and downs of our work, some things remain. Equally important is the individual consideration of each person on your team. One of the key characteristics of transformational leaders is their ability to consider the individual, their needs, their motivations, and their weaknesses. Small development plans that help individuals capture their learning and craft their current tasks can go a long way.
2. Challenge growth and be hungry for opportunities: When comparing the skillsets of average managers to top mangers, we see the giving and asking for feedback as a key differentiator. Feedback not only gives individual’s the data they need to accurately assess how they’re doing, but it also allows us to see the challenges we have to overcome. In other words, feedback helps to keep our eyes out for growth opportunities. Some of our greatest learning happens when we are at the edge of what we know. Meaning, the times where learning may be the greatest is when our comfort is pushed and our frameworks are shaky. These moments are often called stretch assignments, and environments where people fail and grow are marked by them.
3. Show up! Be accessible and have people’s backs: To lean on others in failure admittedly requires those others are there to be leaned upon. It is one thing to communicate a value of support. A whole other thing to actually be there to support. This means that leaders must model receptiveness to feedback and model having people’s back. Having people’s back may be providing feedback, it may mean asking about someone’s family, and it may mean looking out for stretch opportunities. You can test yourself on how you might be doing by asking, “If the people I am responsible for were asked, ‘How does your manager have your back?’ what would you hope they’d say?” The answer to that question could be a great place to start your own development plan.

And as a final note, communicating that you are both invested and listening can speak volumes. Here’s a ridiculously simple example to illustrate. After communicating feeling disconnected from my team in NY, one of my colleagues downloaded and invited me to use an app called Voxer (not a plug, but really, it’s the shit). This simple walky talky app keeps us connected despite of dispersed locations.

One of my favorite meta lessons from using this is the message that appears below your sent messages that says, “heard.” With this one word icon, I am able to feel what we all desire each day. To feel heard. Seen. Noticed. How often do we speak to those who should have our development as their focus, and wonder, did they hear me? Did they understand? Do they care? Without being heard, it’s pretty difficult to feel like failure might be ok.

So my encouragement to all of you whether you are a leader or not, is to show up for the people around you and see if you can’t help cultivate the grit they need to get through the valley.